The Ledger
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Awotona: Calendly's top sales competition is its own free plan
“If you talk to a sales rep at Calendly, Their number one competition is not, you know, any of the competitors that they mentioned, it's the free.”
Awotona: Calendly will stay single-product for a long time
“In our case, like, you know, we have a single product and we'll, we will for a very long time, and part of the reason that we've been able to do that and still grow and become a unicorn and still, like, grow at a pretty fast pace is really expanded the types o…”
Awotona: Calendly defines user activation as five completed bookings
“I start sending my links to people to schedule with me. And five people have scheduled with me is what we define as activated.”
Awotona: Calendly's viral conversion rates declined at scale
“We've definitely seen the, yes, you see the, those conversion rates decline. But the good thing is like the top line, the denominator is getting bigger.”
Awotona: Calendly spends almost zero dollars on marketing campaigns
“We spend almost zero dollars on, we have headcount in marketing, but we have almost zero dollars in marketing campaigns.”
Awotona: Expanding Calendly's enterprise sales team initially cannibalized its self-serve business
“We expanded that sales team greatly and sure enough, revenue grew. The number of accounts over a hundred K in revenue in revenue also grew, but what we found was the growth in our customer acquisition costs outpaced the incremental revenue growth. And so essen…”
Awotona: Calendly has never cut free tier features since 2014
“Besides then, I don't think we've ever taken anything away from the free plan. Yeah, I think we've all. Yeah, I don't think we've ever taken anything away from the free plan. We've only made the free plan more generous. I'm sure somebody will test my memory, b…”
Awotona: About 90% of Calendly's revenue is self-serve
“It has evolved a lot during the course of our business, but today about 90% of our revenue is self-serve.”
Awotona: Sales-led Calendly customers drove significantly higher retention and NDR
“The reason we lean into that motion is because we observe that those customers who came in through the sales process had just very, very different retention mechanism qualities. They also have very, very different NDR qualities. They expanded it a lot further.”
Awotona: A Few Hundred Million Unique People Have Used Calendly
“But a few hundred million unique people have used their product by now.”
Awotona: Calendly shifted engineering resources heavily toward enterprise from 2020 onward
“From, I would say maybe from twenty-twenty to, twenty-twenty onwards, we made that asymmetric, so we allocated a lot more to that enterprise. Then we did PLG.”
Awotona: External-Facing Roles Make Up About 25% of Business Headcount
“And globally, that looks like, you know, 25% of the, typically, you know, about 25% of the headcount in a business is doing those activities.”
Awotona: Organizing SaaS product teams by capability works better than tier segmentation
“The most, probably the most permanent design that we've had is really organizing the team by those different capabilities and then having them own those problems from, for individuals all the way through enterprise.”
Roberge: PLG requires fast time to value and fails for org operating systems
“The reason it probably didn't work is there needs to be a low time and effort to value use case, and Lattice is like an operating system. It's not something like a single person is going to download and start using it, like a Dropbox or a Calendly”
Ahlering: Verbal enterprise commitment is less than half the battle
“Getting an enterprise company to commit to investing in you is, like, literally less than half the battle. Getting through monstrous MSAs, getting through InfoSec questionnaires, and getting through the paper process at these organizations, Really becomes the …”
Awotona: Category creators can always borrow playbooks from indirect predecessors
“In almost every single thing you're looking to do, somebody has done it before. Maybe not directly in your category, maybe not directly in your space, but there's a very, very clear example that, ah, that you can follow. And so I would look for those parallels…”
Awotona: Calendly would not have reached unicorn scale without PLG
“There's no doubt that I would not be sitting on this stage if Calendar did not, ah, you know, ah, use the PLG model. There's no doubt about that. I mean, we're, we've grown really fast because of that.”
Cummings: Invested $350K as sole pre-revenue investor in Calendly on the spot
“And right there on the spot, I wrote him a check for 350,000 dollars as the sole pre-revenue investor, and today Calendly is used by millions and millions of people around the world.”
Lemkin: Calendly is well over $200 million in revenue
“When you heard him say multi-product, they're well over two hundred million. I don't know where they are. I don't know if they're past 300, but they're well over two hundred million.”
Awotona: Enterprise IT outside regulated sectors no longer views Calendly as rogue
“If you get into the highly regulated industries, financial services, healthcare, there are some that initially perceive us as kind of being a rogue app. And so we have to go through, you know, very rigorous security reviews and things like that. But outside of…”
Awotona: Calendly routes leads between sales and self-serve by company size
“What we essentially use the size of the company to approximate like what we think the total opportunities is within that account. And that's really how we determine, maybe I'm sharing too much about how we route deals between self-serve and to into the sales t…”
Awotona: Calendly plans to release proactive meeting suggestion features this year
“What we're not good at today, what we don't really do much of is like helping you think about who you should be meeting with that you haven't already told us to meet with. So we're working on that. I think towards the end of the year, you'll see us make some i…”
Hott: Slack, Webflow, and OpenAI paid early sales reps full salary
“We did this at Slack, Webflow, OpenAI, and I know many other greats have done it like Calendly, New Relic, and Airtable.”
Ahlering: Calendly raised a $300M Series B at $100M ARR
“When I joined Calendly, we had just completed our series B. We took three hundred million in venture and we were at about a hundred million in ARR.”